Chemoenzymatic Synthesis of Carbohydrates

1Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, 

2 Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC, USA 

Glycochemical Synthesis Strategies and Applications, First Edition. 

Edited by Shang-Cheng Hung and Medel Manuel L. Zulueta. 

FIGURE 9.1 Nucleotide sugar substrates for GTases. CMP, cytidine monophosphate GDP, guanidine diphosphate UDP, uridine diphosphate. 

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H. J. M. Gijsen, L. Qiao, W. Fitz, and C.-H. Wong. Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics, Chem. Rev. 96 443 (1996). 

The GAG synthase enzymes are found in a variety of organisms including all animals fi om hydras to humans, certain pathogenic bacteria, and at least one virus. However, with respect to chemoenzymatic synthesis of carbohydrates, the... 

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Chemoenzymatic and Bioenzymatic Synthesis of Carbohydrate Containing Natural Products... 

Vasiliu D, Razi N, Zhang Y, Jacobsen N, AlUn K, Liu X, Hoffmann J, Bohorov O, BUxt O. Large-scale chemoenzymatic synthesis of blood group and mmor-associated poly-N-acetyllactos-amine antigens. Carbohydr. Res. 2006 341 1447-1457. 

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Chemoenzymatic carbohydrate synthesis has been emerging as an extremely powerful tool to obtain complex oligosaccharides. Chemoenzymatic synthesis has many potential advantages, of which the most significant ones are probably that it offers perfect stereoselectivity and renders the tedious work of synthesizing various selectively protected monosaccharide units unnecessary. It also makes the most difficult glycosylation reactions seem easy (86). Chemoenzymatic synthesis of oligosaccharides is out of the scope of this chapter, but it was the topic of many excellent reviews (73,87-89). 

Zhang J, Kowal P, Fang J, Andreana P, Wang PG. Efficient chemoenzymatic synthesis of globotriose and its derivatives with a recombinant a-(1 4)-galac-tosyltransferase. Carbohydr Res 2002 337 969-976. 

Yan F, Wakarchuk WW, Gilbert M, Richards JC, Whitfield DM. Polymer-supported and chemoenzymatic synthesis of the Neisseria meningitidis pentasaccharide a methodological comparison. Carbohydr Res 2000 328 3-16. 

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